Molar efficiency study of chlorinated NPG substitutes in dentin bonding

This study evaluated and compared the contributions to dentin adhesive bonding of three N-phenylglycine analogues with electron-withdrawing substituents on the aromatic ring. These electron-deficient "N-compounds" included: N-(4-chlorophenyl)-glycine (NCPG), N-methyl-N-(4-chlorophenyl)-glycine (NMNCPG), and N-(3,4-dichlorophenyl)-glycine (NDCPG). An experimental three-step dentin-bonding protocol that consisted of sequential application of acidic ferric oxalate solution, an N-compound in acetone, and a surface-active comonomer in acetone was used. The first and third steps were held constant throughout the study. Each N-compound (NCPG, NMNCPG, NDCPG) was used in step two at ten concentrations ranging from 0.0 mol/L (pure acetone) to 5 x 10(-1) mol/L, depending on solubility. After overnight storage in distilled water, the dentin-to-composite bonds were broken in tension. The data were analyzed with ANOVA, and multiple comparisons were performed with Duncan's Multiple Range test. All statistical tests were controlled at alpha = 0.05. At 5 x 10(-3) mol/L, the relative effectiveness of the three N-compounds (as measured by tensile bond strengths) was NMNCPG > NCPG > NDCPG. Of all concentrations studied, the mean bond strengths produced with NMNCPG were statistically as good as or better than those produced by the other two compounds, and NCPG was always as good as or better than NDCPG. Increased electron-withdrawing from the nitrogen of the amine group by the substituents narrowed the effective concentration range for dentin bonding and, in general, produced lower mean bond strengths between dentin and composite.